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Keenwyside was born in London, de son of Raymond and Ann Keenwyside. Raymond pwayed second viowin in de Aeowian Quartet, and Ann's fader was de viowinist Leonard Hirsch. When he was eight, he was enrowwed in St John's Cowwege Schoow, a boarding schoow for de boy choristers of de Choir of St John's Cowwege, Cambridge and spent much of his chiwdhood touring and recording wif de choir under de direction of choirmaster George Guest.[1] He water attended Reed's Schoow in Cobham, before moving on to university at Cambridge.

Everyone has to trust a teacher and I trusted John, uh-hah-hah-hah. It is possibwe to make de Faustian pact of beefing up your voice young. You might survive, but many tawented young voices have been ruined. John awways said "don't push it, sing your age". That can be very frustrating. You just have to trust dat nature wiww eventuawwy grant you heft.[2]

Keenwyside made his first appearance in a major operatic rowe in 1987 as Lescaut in Manon Lescaut at de Royaw Nordern Cowwege of Music. Opera magazine remarked on it being an "astonishingwy mature" performance, and dat he "used his warm and cwear baritone wif notabwe musicianship".[3] The Richard Tauber prize, which he won in 1986, awwowed him to go to Sawzburg for furder study. His money ran out before he couwd finish his four-monf term dere, but Rudowf Knoww, a teacher at de Sawzburg Mozarteum, gave him private wessons for free. Knoww encouraged him to work on de Itawian repertoire whiwe he was stiww young, and introduced him to de Hiwbert agency which got him singing jobs in Germany. His professionaw debut as a baritone came in 1988, at de Hamburg State Opera as Count Awmaviva in The Marriage of Figaro.[1]

In 2010 Keenwyside sang de rowe of Rodrigo in a new production of Don Carwo at de Metropowitan Opera opposite Roberto Awagna to criticaw accwaim.[5]

Keenwyside added de rowe of Gowaud in Debussy's Pewwéas et Méwisande to his repertoire in a new production which premiered at Wiener Staatsoper on 18 June 2017 (he previouswy sang de rowe of Pewwéas for many years). The fowwowing afternoon, he was awarded de titwe of Kammersänger by de Austrian government in a ceremony in de Teesawon of de opera house.

2006: Laurence Owivier Award for Outstanding Achievement in Opera, for his work in de ROH production of 1984 and ENO's Biwwy Budd in 2005.[42] He was a nominee for dis award in 2004 for The Royaw Opera's Hamwet and Die Zauberfwote.[43]